Publication: Comparison of a Pair of Synthetic Tea-Catechin-Derived Epimers: Synthesis, Antifolate Activity, and Tyrosinase-Mediated Activation in Melanoma
Authors
Sáez Ayala, Magalí ; Chazarra Parres, Soledad ; Tárraga Tomás, Alberto ; Cabezas Herrera, Juan ; Montenegro Arce, María Fernanda ; Rodríguez López, José Neptuno ; Sánchez del Campo Ferrer, Luis
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Publisher
WILEY
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DOI
10.1002/cmdc.201000482
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info:eu-repo/semantics/article
Description
This document is the Accepted Manuscript version of a Published Work that appeared in final form in CHEMMEDCHEM. To access the final edited and published work see https://doi.org/10.1002/cmdc.201000482
Abstract
Despite bioavailability issues, tea catechins have emerged as promising chemopreventive agents because of their efficacy in various animal models. We synthesized two catechin-derived compounds, 3-O-(3,4,5-trimethoxybenzoyl)-(-)-catechin (TMCG) and 3-O-(3,4,5-trimethoxybenzoyl)-(-)-epicatechin (TMECG), in an attempt to improve the stability and cellular absorption of tea polyphenols. The antiproliferative and pro-apoptotic activities of both compounds were analyzed with various cancer cell systems, and TMCG, which was easily synthesized in excellent yield, was more active than TMECG in both melanoma and non-melanoma cell lines. TMCG was also a better inhibitor of dihydrofolate reductase and was more efficiently oxidized by tyrosinase, potentially explaining the difference in activity between these epimers.
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Citation
ChemMedChem, Volumen: 6, Nº: 3, año 2011
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